Hair dye composition containing 2-hydroxy-1,4-naphthoquinone



United States Patent Ice 3,415,601

Patented Dec. 10, 1968 Example 1 3,415,607 The dye prepared in the composition set forth below HAIR DYE COMPOSITION CONTAINING 2 HYDROXY IANAPHTHOQUINONE is found to be capable of imparting a blue color to the Stanley Brechner, West Orange, and Kathleen De Vito, 5 ham Union, N.J., assignors to Warner-Lambert Pharmaceu- Parts by tical Company, Morris Plains, N..I., a corporation of Ingredlent: Percent Delaware Lawsone 0.50 No Drawing. Filed Mar. 1, 1965, Ser. No. 436,267 Monoethanolamine 2.04 1 Claim. (Cl. 8-101) Denatured alcohol (S.D.A. #40) 1.63 10 Benzyl alcohol 5.20

Ammonium lauryl sulfate (Sipon vL-22 by Al- ABSTRACT OF THE DISCLOSURE colac Chemical Corp.) 0.15

A hair dye prepared by reacting a naphthoquinone Hydfoxyethyl cellulose (Natl'osol 250-HR y with a mono-lower alkanol amine. Hercules Powder 'P-) Water, Q.s to 100.00.

This invention relates to certain cosmetic compositions Example 2 capable of imparting color to keratinous fibers and more Th d prepared i th composition t f th b l w P ar y to new and novel y p y in such is found to be capable of imparting a red color to the compositions. hair:

Numerous compositions capable of imparting color to Parts by weight, keratinous fibers have been developed. However, these I di t; nt various compositions are typically characterized by in- Lawsone 3,20 herent disadvantages such as fading off-color in sunlight, Monoethanolarnine 9,84 staining of skin as well as possible toxic effects, the latter Glacial acetic acid 65.60 of which is especially characteristic of the oxidation type W t t ak 100.00 dyes.

It has now been found, however, that new dyes may Examp 1e 3 be prepared by reacting selected naphthoquinones with The dye prepared in the composition set forth below particular amines to form dyes useful for imparting color is found to be capable of imparting a greenish-blue color to keratinous fibers. to the hair:

It is anJobject of this invention, therefore, to provide a Parts by weight, new class of dyes prepared by reacting selected naphtho- Ingredient: percent quinones with particular amines for use in imparting color Lawsone 8.80 to keratinous fibers. Monoethanolamine 3.21

I is 3180 an object of this invention to provide com- Water to make 100-00 positions containing new dyes particularly adapted to impart color to keratinous fibers. Example 4 It is a further object of this invention to provide new, The dye prepared in the composition Sgt f th below stable dyes and compositions containing such dyes for use i fou d to be capable of imparting a, blue color to the in coloring human hair. hair;

Other objects and advantages will become more apparts by weight, parent from the following detailed description. Ingredient; Percent According to the present invention, new dyes are pre- Lawsone 9 pared by reacting selected naphthoquinones with particu- Monomethylamine 435 lar amines to form useful red, brown, green, and blue dyes Water to make 10030 of unestablished constitution useful for coloring keratinous fibers such as animal and human hair. Example 5 The present dyes may be prepared by simple reaction of a naphthoquinone such as Z-hydroxy-1,4-naphthoquinone The dye prepared in the composition set forth below (lawsone), S-hydroxy-1,4-naphthoquinone (juglone) and is found to be capable of imparting a blue-green color 1,4-naphthoquinone with suitable mono-lower alkanol to the hair: amines such as, for example, monomethanolamine, mono- Parts by weight, ethanolamine, monoisopropanolarnine and the like. The Ingredient: percent condensation product so formed is found to be particu- Lawsone 6.13 larly advantageous in coloring keratinous fibers while pos- Monoethanolamine 6.13 sessing high stability in hair coloring compositions. These Ethylene glycol monoethyl ether (Cellosolve hair coloring compositions may be in the form of any by Union Carbide Chemical Co.) 85.90 desirable carrier such as foam for optimum distribu- Pyridine 1.84 tion, spray, liquid, paste or the like. It has also been found that the present dyes may be blended in a hair Example 6 coloring composition, if desired, to provide various shades The dye prepared in the composition Set fo th below and tints.

is found to be capable of imparting a brown color to the The amount of dye WhlCh has been found satisfactory hair:

for use in hair coloring compositions falls within the range Parts by weight, of about 0.005% to about 2.5% by we1ght of the final Ingredient; percent composition which may include typical components known Lawsone 5 7 to the art. Monoisopropanolamine 5.58 In order to more fully illustrate the present invention, Sodium hydroxide 0.59

the following examples are included: Water to make 100.00

3 Example 7 The dye prepared in the composition set forth below is found to be capable of imparting a brown color to the hair:

The novel hair coloring compositions of the present invention are adapted for convenient home use by the consumer. Prior to using any one of these compositions the hair preferably is given a thorough cleansing treatment by washing with a good quality non-soap shampoo. After substantially all dirt, grease and the like has been removed a lustrous new hair color may be obtained upon a single application of the composition herein described.

The addition of various adjuvant materials to the novel hair coloring compositions is contemplated by the present invention. Thus, the compositions ordinarily will contain a perfume which should be selected so as to be compatible with the character of the finished product. Also, the ingredients which impart further desired qualities to the hair may be incorporated in the present compositions. Hair conditioners, for example, or superfatting materials or foam boosters such as lanolin, lecithin, fatty amides, etc., generally may be used in minor proportions. Furthermore, small amounts of thickening agents such as sodium alginate may be included to reduce the fluidity of the product. Moreover, suitable preservatives may be incorporated in minor amounts as need to prevent or substantially minimize the formation of mold.

It is to be understood that the foregoing detailed description is given merely by way of illustration and that many variations may be made therein without departing from the spirit of this invention.

What is claimed is:

1. A dye composition capable of imparting a greenishblue color to the hair which comprises,

Approximate parts Ingredient: by weight, percent 2-hydroxy-4-naphthoquinone 8.80 Monoethanolamine 3.21 Water to make 100.00

References Cited UNITED STATES PATENTS 1,759,273 5/1930 Nawiasky et al. 260-396 2,745,788 5/1956 Frohnsdorfi et al 167-88 3,041,244 6/1962 Feit et al l6788 3,092,555 6/1963 Horn 167-88 3,114,755 12/1963 Covey 260-396 3,147,288 9/ 1964 Frohnsdorff 16788 X 3,251,744 5/1966 Brunner 167--88 FOREIGN PATENTS 304,804 1/ 1929 Great Britain. 826,479 1/ 1960 Great Britain. 919,824 2/1963 Great Britain. 1,138,955 2/1957 France.

ALBERT T. MEYERS, Primary Examiner. V. C. CLARKE, Assistant Examiner.

US. Cl. X.R. 810, 11 

